hexan-2-yl benzoate | 59614-01-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: hexan-2-yl benzoate
• 英文别名: Benzoic acid, hex-2-yl ester
• CAS: 59614-01-6
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: RDZOLJBSUTTYRO-UHFFFAOYSA-N

物化性质

• 保留指数：
  1512

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-hexen-2-yl benzoate 在 1,1'-bis(diisopropylphosphino)ferrocene(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 氢气 作用下， 以 二氯甲烷 为溶剂， 40.0 ℃ 、400.01 kPa 条件下， 反应 24.0h， 生成 hexan-2-yl benzoate
  参考文献：
  名称：

  1-烷基乙烯基苯甲酸酯的高度对映选择性加氢：手性2-烷基醇的简单，非酶促途径

  摘要：

  走向手性！描述了通过使用带有P bearingOP配体的Rh催化剂对烯醇酯1的高度对映选择性催化氢化（参见方案； NBD ＝降冰片二烯）。该催化体系具有广泛的范围，并允许制备具有高对映选择性的各种带有各种烷基或苄基的手性酯2。这些酯可以很容易地转化为高度对映体富集的2-链烷醇。

  DOI：

  10.1002/chem.201303500

文献信息

• A facile method for the oxidative removal of benzyl ethers: the oxidation of benzyl ethers to benzoates by ruthenium tetraoxide
  作者：Paul Francis Schuda、Melissa B. Cichowicz、Martha R. Heimann

  DOI：10.1016/s0040-4039(00)94286-2

  日期：1983.1

  A series of benzyl ethers has been prepared and their oxidation to benzoates esters by ruthenium tetraoxide has been studied. Yields for the oxidation step range from 54 to 96%.

  已经制备了一系列苄基醚，并且已经研究了它们被四氧化钌氧化为苯甲酸酯的方法。氧化步骤的产率为54％至96％。
• Esterification of free fatty acids (Biodiesel) using nano sulfated-titania as catalyst in solvent-free conditions
  作者：Mona Hosseini-Sarvari、Esmat Sodagar

  DOI：10.1016/j.crci.2012.10.016

  日期：2013.3

  Résumé Nano sulfated titania was tested as catalyst for esterification of free fatty acids, specially methanolic and ethanolic esterification of stearic acid (biodiesels). Factorial design evidenced a positive effect of reaction temperature, amount of catalyst, and solvents on ester conversion. This nano-sized sulfated titania has been prepared by a sol-gel hydrothermal process. This prepared sulfated titania showed high catalytic activity in direct esterification of fatty acids as well as benzoic acids with various alcohols and phenols under solvent-free conditions. This method is of great value because of its environmentally benign character, easy handling, high yields, convenient operation, and green. FT-IR studies are shown that the catalyst can be reused for acylation without loss of catalytic activity.

  简历 纳米硫酸盐钛被测试为自由脂肪酸酯化的催化剂，特别是硬脂酸（生物柴油）的甲醇和乙醇酯化。实验设计表明，反应温度、催化剂用量和溶剂对酯转化率有正向影响。这种纳米尺寸的硫酸盐钛是通过溶胶-凝胶水热法制备的。制备的硫酸盐钛在无溶剂条件下显示出高催化活性，能直接酯化脂肪酸以及各种醇和酚的苯甲酸。这种方法因其环境友好、易于操作、高产率、操作简便和绿色特性而具有重要价值。傅里叶变换红外光谱研究表明，催化剂可在不损失催化活性的情况下重复用于酰化反应。
• Base-catalyzed selective esterification of alcohols with unactivated esters
  作者：Chunyan Zhang、Guoying Zhang、Shizhong Luo、Chunfu Wang、Huiping Li

  DOI：10.1039/c8ob02411a

  日期：——

  A practical and efficient base-catalyzed esterification has been developed for the facile synthesis of a broad range of esters from simple alcohols with unactivated tert-butyl esters. This protocol could be conducted at mild conditions, providing esters in high to excellent yields with good functional tolerance. Mechanistic studies provided evidence of an exchange of the tert-butyl alkoxide metal with

  已经开发了一种实用且有效的碱催化的酯化反应，用于从简单的醇与未活化的叔丁酯容易地合成多种酯。该方案可以在温和的条件下进行，以高至优异的产率提供酯，具有良好的功能耐受性。机理研究提供了叔丁基醇盐金属与醇交换的证据，产生了新的醇盐参与酯交换反应。
• Epoxide as precatalyst for metal-free catalytic transesterification
  作者：Shinji Tanaka、Takuya Nakashima、Naoto Satou、Hiromi Oono、Yoshihiro Kon、Masanori Tamura、Kazuhiko Sato

  DOI：10.1016/j.tetlet.2019.06.056

  日期：2019.7

  Transesterification of methyl esters was accelerated by an in situ-generated metal-free catalyst comprising a quaternary alkylammonium salt and an epoxide. The combination of a quaternary alkylammonium acetate and glycidol is optimal, and various esters were synthesized from methyl esters with alcohols in good to excellent yield. Analysis of the catalyst solution revealed that basic species are generated

  通过原位生成的包含季烷基铵盐和环氧化物的无金属催化剂促进了甲酯的酯交换反应。乙酸季烷基铵和缩水甘油的组合是最佳的，并且由甲基酯与醇合成各种酯，收率良好至极佳。催化剂溶液的分析表明，碱性物质是由环氧化物的开环反应产生的。
• Understanding in Vivo Benzenoid Metabolism in Petunia Petal Tissue
  作者：Jennifer Boatright、Florence Negre、Xinlu Chen、Christine M. Kish、Barbara Wood、Greg Peel、Irina Orlova、David Gang、David Rhodes、Natalia Dudareva

  DOI：10.1104/pp.104.045468

  日期：2004.8.1

  In vivo stable isotope labeling and computer-assisted metabolic flux analysis were used to investigate the metabolic pathways in petunia (Petunia hybrida) cv Mitchell leading from Phe to benzenoid compounds, a process that requires the shortening of the side chain by a C2 unit. Deuterium-labeled Phe (2H5-Phe) was supplied to excised petunia petals. The intracellular pools of benzenoid/phenylpropanoid-related compounds (intermediates and end products) as well as volatile end products within the floral bouquet were analyzed for pool sizes and labeling kinetics by gas chromatography-mass spectrometry and liquid chromatography-mass spectrometry. Modeling of the benzenoid network revealed that both the CoA-dependent, β-oxidative and CoA-independent, non-β-oxidative pathways contribute to the formation of benzenoid compounds in petunia flowers. The flux through the CoA-independent, non-β-oxidative pathway with benzaldehyde as a key intermediate was estimated to be about 2 times higher than the flux through the CoA-dependent, β-oxidative pathway. Modeling of 2H5-Phe labeling data predicted that in addition to benzaldehyde, benzylbenzoate is an intermediate between l-Phe and benzoic acid. Benzylbenzoate is the result of benzoylation of benzyl alcohol, for which activity was detected in petunia petals. A cDNA encoding a benzoyl-CoA:benzyl alcohol/phenylethanol benzoyltransferase was isolated from petunia cv Mitchell using a functional genomic approach. Biochemical characterization of a purified recombinant benzoyl-CoA:benzyl alcohol/phenylethanol benzoyltransferase protein showed that it can produce benzylbenzoate and phenylethyl benzoate, both present in petunia corollas, with similar catalytic efficiencies.

  采用体内稳定同位素标记和计算机辅助代谢通量分析，研究了从苯丙氨酸到苯环化合物的代谢途径，这个过程需要将侧链缩短一个C2单元的方式。氘标记的苯丙氨酸（2H5-Phe）被提供给切除的矮牵牛（Petunia hybrida）Mitchell品种的花瓣。通过气相色谱-质谱和液相色谱-质谱分析花香中的苯环/苯丙素相关化合物（中间产物和终产物）以及挥发性终产物的细胞内库大小和标记动力学。苯环网络的建模表明，CoA依赖性β氧化和CoA非依赖性非β氧化途径都对矮牵牛花中苯环化合物的形成做出了贡献。以苯甲醛为关键中间体的CoA非依赖性非β氧化途径通量估计约为CoA依赖性β氧化途径通量的2倍。2H5-Phe标记数据的建模预测，除了苯甲醛外，苄基苯甲酸酯是L-苯丙氨酸和苯甲酸之间的中间体。苄基苯甲酸酯是苄基醇苯甲酰化的产物，在矮牵牛花瓣中检测到了其活性。利用功能基因组学方法，从矮牵牛Mitchell品种中分离了编码苯丙醇/苄醇苯甲酰转移酶的苯乙酰-CoA：苄醇/苯乙醇苯甲酰转移酶的cDNA。对纯化重组苯乙酰-CoA：苄醇/苯乙醇苯甲酰转移酶蛋白的生化特性进行了表征，表明它可以产生苄基苯甲酸酯和苯乙基苯甲酸酯，两者在矮牵牛花冠中具有类似的催化效率。